Hair Transformations: Kate Upton, Kylie Jenner

There is a lesson for aspiring musicians to be learned from Swift's ascent, and that is to hit the road and work on your songwriting as much as you do your voice.

Swift's 2011 tour snagged her $29 million, and the fact that she wrote all 14 songs on her quadruple-platinum-selling album "Speak Now" (and therefore earns songwriter royalties) explains how she earned the #1 spot.